Water → HCID 57111540, compound

HRID 1252528Notes

Reaction equation

HRID 1252528 reaction equation
[NH2:1][C@@H:2]([CH2:27][C:28](=[O:47])[NH:29]C(C1C=CC(OC)=CC=1)C1C=CC(OC)=CC=1)[C:3]([NH:5][C@@H:6]([C@H:10]([NH:12][C@H:13]([C:24]([OH:26])=[O:25])[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)[CH3:11])[C:7]([OH:9])=[O:8])=[O:4].C1(OC)C=CC=CC=1.O.C(OCC)(=O)C>FC(F)(F)C(O)=O>[NH2:1][C@@H:2]([CH2:27][C:28](=[O:47])[NH2:29])[C:3]([NH:5][C@@H:6]([C@H:10]([NH:12][C@H:13]([C:24]([OH:26])=[O:25])[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)[CH3:11])[C:7]([OH:9])=[O:8])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 7519AnisoleHCID 8857Ethyl AcetateHCID 57269490HCID 57269490, compound

Product 1

HCID 57111540HCID 57111540, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (2S,3R)-2-[[(2S)-2-amino-3-[N-[bis(4-methoxyphenyl)methyl]carbamoyl]propionyl]amino] 3-[[(1S)-1-carboxy-2-(3 indolyl)ethyl]amino]butyric acid (427 mg) in a mixture of trifluoroacetic acid (3 ml), anisol (0.5 ml) and ethaneditiol (0.1 ml) was stirred overnight at room temperature and the mixture was poured into a mixture of water (10 ml) and ethyl acetate (10 ml). The aqueous phase was separated and subjected to a column of Dowex 50W x 8 (H+, 20 ml). The column was washed with water and the elution was carried out with 2.8% aqueous ammonia. The object fractions were collected and evaporated in vacuo. To the residue was added water and the mixture was lyophilized to give (2S,3R)-2-[[(2S)-2-amino-3-carbamoylpropionyl]amino]3-[[(1S)-1-carboxy-2-(3-indolyl)ethyl]amino]butyric acid (85 mg) as a pale brown powder.

Workup

  1. customThe aqueous phase was separated
  2. washThe column was washed with water
  3. washthe elution
  4. customThe object fractions were collected
  5. customevaporated in vacuo
  6. additionTo the residue was added water

Sources & evidence

ORD record
ord-399d3be0bb3d483db03a489b96d4cb8a
Source dataset
uspto-grants-1988_05
Patent number
US04743614

Reaction notes

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